CN113788805B - Method for synthesizing hydroxymethylfurfural through lactose conversion - Google Patents
Method for synthesizing hydroxymethylfurfural through lactose conversion Download PDFInfo
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Abstract
The invention discloses a method for synthesizing Hydroxymethylfurfural (HMF) by lactose conversion, relates to a biomass resource conversion method in the field of alternative energy, and aims to provide a method for synthesizing Hydroxymethylfurfural (HMF) by catalysis in a liquid phase system. Relates to a catalytic conversion process of lactose, aims to obtain HMF, and belongs to the field of biomass resource conversion and utilization. The method adopts metal salt as a catalyst, and can effectively convert lactose into HMF in an ionic liquid system with high water content. The method is simple to operate, the yield of the obtained HMF is higher, and the dosage of the ionic liquid in the solvent is obviously reduced compared with that in the existing research process. The information provided by the present process may provide a useful reference for the conversion of lactose-rich biomass resources.
Description
Technical Field
The invention relates to a biomass resource conversion synthesis method in the field of alternative energy, in particular to a method for synthesizing hydroxymethylfurfural by lactose conversion.
Background
Traditional fossil energy sources mainly comprise petroleum, coal and natural gas, and play an important role in the development process of the world, and global development is seriously dependent on fossil energy sources. However, these three energy sources are not renewable and with the rapid development of the world for many years, a large amount of fossil energy sources are consumed and a large amount of greenhouse gases are emitted, which is a serious challenge for the sustainable development in the future. Development and utilization of new renewable energy sources is an effective measure to alleviate the global serious dependence on fossil-like energy sources and to reduce greenhouse gas emissions.
Biomass resources have been considered as a very promising alternative energy source in recent years. Biomass reserves are very rich, mainly comprise terrestrial and aquatic plants, are widely distributed and have low pollution. These plants are able to store solar energy in the form of chemical energy by photosynthesis. The biomass resources used in the current research field mainly refer to lignocellulose, and the main components of the biomass resources are cellulose, hemicellulose and lignin respectively. The lignocellulose is fully utilized and converted into some commodity with potential of replacing petrochemicals, and the commodity has an important supporting effect on sustainable development.
Hydroxymethylfurfural (HMF) is a popular platform compound in recent years, attracting extensive research attention. First, HMF has different kinds of functional groups in its chemical structure, for example, hydroxymethyl and aldehyde groups at the 2-and 5-positions of its chemical structure, respectively, and itself has a furan ring, which makes its chemical properties flexible and variable. Second, HMF can be converted to a range of downstream chemicals with high added value by a variety of different processes. For example, 2, 5-dimethylfuran obtained by selective hydrogenation can be used as a liquid fuel, 2, 5-furandicarboxylic acid obtained by selective oxidation can be used for preparing a polymer compound, and a series of products obtained by reductive amination can be used for synthesizing a pharmaceutical intermediate or a polymer compound. Finally, HMF can be obtained by selective dehydration conversion of hexoses or their polymers. These sugars are renewable biomass resources, which is a realistic basis for advancing biomass conversion processes typified by HMF.
At present, the research field mainly relates to the selective conversion of fructose and glucose to synthesize HMF. The conversion of fructose is relatively easy, the fructose can be converted into HMF in a plurality of solvent systems under the action of a plurality of catalysts, and the yield of the obtained HMF is high. Glucose conversion is difficult compared to fructose because glucose exists primarily as a six-membered pyran ring structure, which is less active in conversion. Fructose is generally present in about 30% of five-membered furan ring structures, which have a high conversion activity. The conversion of glucose generally requires first undergoing an isomerization process to form fructose, and subsequent conversion of the fructose produced to HMF. In addition to fructose and glucose, research attention has been paid to the use of their polymers as raw materials, with the aim of reducing raw material costs.
However, many kinds of saccharide resources have not been studied in nature. The full and efficient utilization of these resources will effectively advance the important supporting role played by biomass resources in future alternative energy fields. In nature, various sugars are not present in a single form, they are often present in the form of polymers of complex structure, and these sugar units often lead to complete differences in conversion activity due to subtle changes in the spatial structure of a certain functional group. Therefore, a detailed study of various conversion processes of saccharide resources has important significance for comprehensive utilization of biomass resources. As mentioned above, fructose and glucose are six-carbon sugar raw materials mainly involved in the current research field, and disaccharides corresponding thereto, such as sucrose, cellobiose, maltose, etc., have also been widely studied. However, there are also carbohydrate resources in nature that are similar to them but still of interest for obtaining attention. Lactose is a disaccharide whose chemical structure is composed of one molecule of galactose and one molecule of glucose. Among them, galactose is a C4 epimer of glucose, which results in a significant difference in chemical conversion activity from glucose. According to current research reports, the yield of HMF obtained as galactose conversion is generally low. As such, lactose also has a low conversion activity due to the presence of galactose building blocks and has not received much attention. Lactose is widely found in the natural world in mammalian milk and is obtained by raising a large number of domestic animals. In addition, a large amount of dairy waste is generated in daily life of human society, so that the possible pollution caused by the waste is solved by fully utilizing the resources, and meanwhile, the high-value utilization of renewable resources is improved, and the method has important significance for supporting sustainable development.
In recent years, a reaction system for synthesizing HMF by converting saccharides mainly comprises water, a water-organic solvent biphasic system, a polar organic solvent, an ionic liquid, a supercritical fluid and the like. Among them, ionic liquids have recently received very extensive attention. The conversion of saccharides in various ionic liquids to obtain HMF has higher yield, which is generally superior to the conversion performance in other solvent systems. However, ionic liquids also have some drawbacks. First, the cost of ionic liquids remains a concern. Second, ionic liquids may be potentially toxic. Thirdly, the ionic liquid has strong water absorption, and extra drying treatment is often needed, so that the operation steps and the process cost are increased. Finally, it has been reported that the absorption of large amounts of water in ionic liquids also significantly inhibits the dehydration of sugars to HMF, resulting in a significant reduction in its yield. Therefore, how to reduce the dosage of the ionic liquid and how to overcome the problems of greatly reduced saccharide conversion performance caused by water absorption of the ionic liquid are some key challenges of the current saccharide conversion synthesis of HMF.
Disclosure of Invention
The invention aims to provide a method for synthesizing hydroxymethylfurfural by lactose conversion, which uses metal salt as a catalyst to effectively convert lactose into Hydroxymethylfurfural (HMF) in an ionic liquid system with high water content, and has higher yield.
The invention aims at realizing the following technical scheme:
a method for synthesizing hydroxymethylfurfural by lactose conversion, which comprises the following preparation processes:
a. adding raw materials, a catalyst, ionic liquid and water into a reaction bottle;
b. placing the reaction bottle filled with the raw materials, the catalyst, the ionic liquid and the water into a reaction module with preset temperature, heating and stirring, and then generating HMF;
the catalyst in the step a comprises chromium trichloride or chromium nitrate or a mixture of the two metal salts;
the molar ratio of the catalyst to lactose in the step a is 1:5-1:2.
The ionic liquid in the step a comprises 1-ethyl-3-methylimidazole chloride, 1-butyl-3-methylimidazole chloride, 1-hexyl-3-methylimidazole chloride, 1-ethyl-3-methylimidazole bromide, 1-butyl-3-methylimidazole bromide, 1-hexyl-3-methylimidazole bromide or a mixture of the ionic liquids.
In the step a, the high-water-content ionic liquid system refers to an ionic liquid and water mixture, wherein the mass fraction of water in the ionic liquid and water mixture is 30% -55%.
The method for synthesizing the hydroxymethylfurfural by converting lactose effectively converts lactose into Hydroxymethylfurfural (HMF) in an ionic liquid system with high water content by taking metal salt as a catalyst.
The invention has the advantages and effects that:
1. the method effectively converts lactose resources widely existing in the nature into the important chemical intermediate of the hydroxymethyl furfural, adopts an ionic liquid system with high water content, can reduce the cost of using the ionic liquid and potential pollution possibly caused by using a large amount of the ionic liquid, can effectively obtain the hydroxymethyl furfural in the system, and emphasizes the lack of water in the system when the ionic liquid system is used. The invention solves the problem that lactose is effectively converted and water in the ionic liquid is negatively influenced. The transformation prospect is good.
2. The water content in the system is higher, the use amount of the ionic liquid can be correspondingly reduced, and the use cost of the ionic liquid is reduced. The water content in the system is higher, so that the use amount of the ionic liquid can be correspondingly reduced, and the potential toxicity and the potential pollution possibly caused by the ionic liquid system are reduced.
3. Since more water is needed to be added into the system, the drying step of the ionic liquid can be reduced.
4. The conversion of lactose to HMF is better and the yield of the product is higher.
Detailed Description
The present invention will be described in detail with reference to examples.
Example 1
60 Lactose mg and chromium trichloride as catalyst (CrCl) 3 ) Adding into a micro-reaction bottle, adding 560 mg ionic liquid 1-ethyl-3-methylimidazole chloride and 240 mg water, crCl 3 The molar amount of (2) is 20% of the molar amount of lactose, at 150 o Reaction 1 h under C, stirring speed 300 r/min, after the reaction, the sample was tested by ultraviolet-visible spectrophotometer, and the yield of HMF was 52%.
Example 2
60 Lactose mg and chromium trichloride as catalyst (CrCl) 3 ) Adding into micro-reaction bottle, adding 480 mg ionic liquid 1-ethyl-3-methylimidazole chloride and 320-mg water, crCl 3 The molar amount of (2) is 20% of the molar amount of lactose, at 150 o Reaction 1 h under C, stirring speed 300 r/min, after the reaction, using an ultraviolet-visible spectrophotometer to test the sample, the yield of HMF was 56%.
Example 3
60 Lactose mg and chromium trichloride as catalyst (CrCl) 3 ) Adding into micro-reaction bottle, adding 480 mg ionic liquid 1-ethyl-3-methylimidazole chloride and 320-mg water, crCl 3 The molar amount of (2) is 30% of the molar amount of lactose, at 150 o Reaction 1 h under C, stirring speed 300 r/min, and after the reaction, testing the sample by using an ultraviolet-visible spectrophotometer, wherein the yield of HMF is 59%.
Example 4
60 Lactose mg and chromium trichloride as catalyst (CrCl) 3 ) Adding into micro-reaction bottle, adding 480 mg ionic liquid 1-ethyl-3-methylimidazole chloride and 320-mg water, crCl 3 The molar amount of (2) is 20% of the molar amount of lactose, 140 o Reaction 2 h under C, stirring speed 300 r/min, after the reaction, the sample was tested by ultraviolet-visible spectrophotometer, and the yield of HMF was 58%.
Example 5
60 Lactose mg and chromium trichloride as catalyst (CrCl) 3 ) Adding into micro-reaction bottle, adding 480 mg ionic liquid 1-butyl-3-methylimidazole bromide and 320-mg water, crCl 3 The molar amount of (2) is 20% of the molar amount of lactose, at 150 o Reaction 1 h under C, stirring speed 300 r/min, after the reaction, the sample was tested by ultraviolet-visible spectrophotometer, and the yield of HMF was 58%.
Example 6
60 Lactose mg and chromium trichloride as catalyst (CrCl) 3 ) Adding into a micro-reaction bottle, adding 480 mg ionic liquid 1-butyl-3-methylimidazole chloride and 320 mg water, crCl 3 The molar amount of (2) is 20% of the molar amount of lactose, at 160 o The reaction under C was carried out at 0.5. 0.5 h and a stirring speed of 300 r/min, and after the reaction was completed, the sample was tested by an ultraviolet-visible spectrophotometer and the yield of HMF was 54%.
Example 7
60 Lactose mg and chromium trichloride as catalyst (CrCl) 3 ) Adding into a micro-reaction bottle, adding 480 mg ionic liquid 1-hexyl-3-methylimidazole chloride and 320-mg water, crCl 3 The molar amount of (2) is 20% of the molar amount of lactose, at 160 o The reaction under C is carried out at 0.5 and h, the stirring speed is 300 r/min, and after the reaction is finished, ultraviolet and visible are utilizedThe sample was spectrophotometrically tested and the yield of HMF was 52%.
Example 8
60 Lactose mg and chromium nitrate catalyst (Cr (NO) 3 ) 3 ) Adding into micro-reaction bottle, adding 480 mg ionic liquid 1-butyl-3-methylimidazole chloride and 320-mg water, cr (NO) 3 ) 3 The molar amount of (2) is 20% of the molar amount of lactose, at 150 o Reaction 1 h under C, stirring speed 300 r/min, after the reaction, the sample was tested by ultraviolet-visible spectrophotometer, and the yield of HMF was 57%.
While the invention has been described with respect to the preferred embodiments, it should be understood that the invention is not limited thereto, but rather is limited thereto, and that the invention is not limited thereto, but rather is intended to cover modifications, substitutions, and other modifications, obvious to those skilled in the art, within the scope of the present invention. Therefore, the protection scope of the present invention should be subject to the protection scope of the claims.
Claims (4)
1. A method for synthesizing hydroxymethylfurfural by lactose conversion, which is characterized by comprising the following preparation processes: 60 Adding lactose and catalyst chromium trichloride into a micro-reaction bottle, adding 480 mg ionic liquid 1-ethyl-3-methylimidazole chloride and 320 mg water, reacting at 150 ℃ for 1 h, stirring at 300 r/min, and testing a sample by using an ultraviolet-visible spectrophotometer after the reaction is finished, wherein the molar quantity of the chromium trichloride is 20% of that of the lactose, and the yield of HMF is 56%.
2. A method for synthesizing hydroxymethylfurfural by lactose conversion, which is characterized by comprising the following preparation processes: 60 Adding lactose and catalyst chromium trichloride into a micro-reaction bottle, adding 480 mg ionic liquid 1-ethyl-3-methylimidazole chloride and 320 mg water, reacting at 150 ℃ for 1 h, stirring at 300 r/min, and testing a sample by using an ultraviolet-visible spectrophotometer after the reaction is finished, wherein the molar quantity of the chromium trichloride is 30% of that of the lactose, and the yield of HMF is 59%.
3. A method for synthesizing hydroxymethylfurfural by lactose conversion, which is characterized by comprising the following preparation processes: 60 Adding lactose and catalyst chromium trichloride into a micro-reaction bottle, adding 480 mg ionic liquid 1-ethyl-3-methylimidazole chloride and 320 mg water, reacting at 140 ℃ for 2 h, stirring at 300 r/min, and testing a sample by using an ultraviolet-visible spectrophotometer after the reaction is finished, wherein the molar quantity of the chromium trichloride is 20% of that of the lactose, and the yield of HMF is 58%.
4. A method for synthesizing hydroxymethylfurfural by lactose conversion, which is characterized by comprising the following preparation processes: 60 Adding lactose and catalyst chromium trichloride into a micro-reaction bottle, adding 480 mg ionic liquid 1-butyl-3-methylimidazole bromide and 320 mg water, reacting at 150 ℃ for 1 h, stirring at 300 r/min, and testing a sample by using an ultraviolet-visible spectrophotometer after the reaction is finished, wherein the molar quantity of the chromium trichloride is 20% of that of the lactose, and the yield of HMF is 58%.
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